Sam and Milo are best friends who work at a Chicago commercial production agency. Sam fixes up Milo on a blind date with an acquaintance named Robyn, and it turns into a disaster. The disaster continues when the two suddenly discover that Robyn has been hired as their new boss.
When the gang decides to set each other up on dates, Robyn is convinced that Milo will hook her up with a loser, so she fixes him up with a very kinky girl. When she realizes her date is a good guy, she feels guilty and tries to save Milo, only to find him in a very compromising position. Meanwhile, Sam thinks his date is a catch, if only she wasn't so clumsy...
When Milo develops a crush on an attractive psychologist who works in the building, he asks her out and ends up in a therapy session. But when he realizes he isn't getting anywhere, he asks Sam to speak to her on his behalf. After Sam pays a visit to the doctor, he and Milo find themselves in a brief boxing match. Meanwhile, Jack enlists Robyn to teach him line dancing for his daughter's birthday party.
Eric, Robyn's ex-boyfriend, comes back to Chicago and to her surprise has landed his own sitcom. When she gets a ticket to the premiere, she refuses to attend...until she finds out that she was the inspriation for the show. When it turns out that the sitcom is based on their past dysfunctional relationship, Robyn turns to the rest of the office for support.
Just when Robyn hits rock bottom because of apartment problems, she gets an invitation to her old rival's bridal shower. Robyn doesn't want to go until she realizes that the woman has an amazing apartment that will be vacant after the wedding. Robyn decides to kiss up and throw a bachelorette party for the bride. The party is a dud, until Robyn enlists the help of Sam and Milo to strip for the ladies.
The gang head off to San Francisco on a business trip -- which quickly leads to pleasure.
Robyn brings down Milo's curtain when she tells him that his bedroom performance with her roommate has forced the poor woman to do some acting herself.
Robyn fantasizes about the men in the office when she is told that the right man for her may be nearby.
Robyn fantasizes about romance with various men at the office.
